Thio-phene-2-carbonyl azide.

The title compound, C5H3N3OS, is almost planar (r.m.s. deviation for the ten non-H atoms = 0.018 Å) and forms an extended layer structure in the (100) plane, held together via hydrogen-bonding inter-actions between adjacent mol-ecules. Of particular note is the occurrence of RC-H⋯N(-)=N(+)=NR inter-actions between an aromatic C-H group and an azide moiety which, in conjunction with a complementary C-H⋯O=C inter-action, forms a nine-membered ring.

Related literature

For a previous preparation of the title compound, see: Binder et al. (1977 ▶). For the synthesis of the starting material, 2-thio­phene­carbonyl chloride, see: Kruse et al. (1989 ▶). For related structures, see: Arsenyan et al. (2008 ▶); Elshaarawy & Janiak (2011 ▶); Low et al. (2009 ▶).

Experimental

Crystal data

C5H3N3OS

M = 153.16

Monoclinic,

a = 12.668 (3) Å

b = 6.2153 (12) Å

c = 16.400 (3) Å

β = 95.91 (3)°

V = 1284.4 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.43 mm−1

T = 153 K

0.20 × 0.16 × 0.15 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (DENZO and SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.920, T max = 0.939

2728 measured reflections

1459 independent reflections

1152 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.154

S = 1.13

1459 reflections

91 parameters

H-atom parameters constrained

Δρmax = 0.59 e Å−3

Δρmin = −0.49 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: COLLECT; data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2013 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXTL, enCIFer (Allen et al., 2004 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813019740/tk5242sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813019740/tk5242Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813019740/tk5242Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C5H3N3OS	F(000) = 624
Mr = 153.16	Dx = 1.584 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.668 (3) Å	Cell parameters from 1494 reflections
b = 6.2153 (12) Å	θ = 1.0–27.5°
c = 16.400 (3) Å	µ = 0.43 mm−1
β = 95.91 (3)°	T = 153 K
V = 1284.4 (4) Å3	Block, colourless
Z = 8	0.20 × 0.16 × 0.15 mm

Nonius KappaCCD diffractometer	1152 reflections with I > 2σ(I)
Radiation source: fine focus sealed tube	Rint = 0.025
φ and ω scans	θmax = 27.4°, θmin = 2.5°
Absorption correction: multi-scan (DENZO and SCALEPACK; Otwinowski & Minor, 1997)	h = −15→16
Tmin = 0.920, Tmax = 0.939	k = −7→8
2728 measured reflections	l = −21→21
1459 independent reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.0659P)2 + 3.253P] where P = (Fo2 + 2Fc2)/3
1459 reflections	(Δ/σ)max = 0.001
91 parameters	Δρmax = 0.59 e Å−3
0 restraints	Δρmin = −0.49 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

	x	y	z	Uiso*/Ueq
C1	0.3676 (2)	0.0373 (4)	0.57926 (15)	0.0260 (6)
C2	0.3494 (2)	−0.1827 (4)	0.59864 (15)	0.0238 (6)
H2	0.3401	−0.2988	0.5609	0.029*
C3	0.3478 (2)	−0.1956 (5)	0.68730 (18)	0.0334 (7)
H3	0.3368	−0.3267	0.7150	0.040*
C4	0.3632 (2)	−0.0048 (5)	0.72675 (17)	0.0347 (7)
H4	0.3647	0.0105	0.7845	0.042*
C5	0.3763 (2)	0.1133 (5)	0.49575 (15)	0.0271 (6)
N1	0.3946 (2)	0.3386 (4)	0.49385 (13)	0.0323 (6)
N2	0.39920 (19)	0.4093 (4)	0.42227 (13)	0.0308 (6)
N3	0.4044 (2)	0.4879 (5)	0.36125 (15)	0.0401 (7)
O1	0.36928 (17)	−0.0003 (4)	0.43538 (12)	0.0382 (5)
S1	0.37950 (6)	0.20165 (12)	0.66320 (4)	0.0360 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0249 (13)	0.0295 (14)	0.0237 (12)	−0.0011 (11)	0.0039 (10)	−0.0039 (10)
C2	0.0247 (13)	0.0226 (13)	0.0248 (12)	0.0005 (10)	0.0062 (10)	0.0053 (10)
C3	0.0358 (16)	0.0308 (16)	0.0340 (15)	−0.0005 (12)	0.0055 (12)	0.0079 (12)
C4	0.0364 (16)	0.0438 (18)	0.0240 (13)	0.0034 (14)	0.0035 (11)	0.0026 (12)
C5	0.0251 (13)	0.0311 (15)	0.0255 (13)	−0.0021 (11)	0.0045 (10)	−0.0028 (11)
N1	0.0438 (14)	0.0336 (13)	0.0196 (11)	−0.0007 (11)	0.0028 (9)	−0.0002 (9)
N2	0.0317 (13)	0.0335 (14)	0.0266 (12)	−0.0035 (10)	0.0002 (9)	−0.0026 (10)
N3	0.0461 (16)	0.0450 (16)	0.0286 (13)	−0.0109 (13)	0.0005 (10)	0.0039 (12)
O1	0.0519 (14)	0.0382 (12)	0.0255 (10)	−0.0086 (10)	0.0080 (8)	−0.0072 (9)
S1	0.0487 (5)	0.0318 (4)	0.0275 (4)	−0.0028 (3)	0.0036 (3)	−0.0018 (3)

C1—C2	1.428 (4)	C4—S1	1.679 (3)
C1—C5	1.464 (4)	C4—H4	0.9500
C1—S1	1.708 (3)	C5—O1	1.212 (3)
C2—C3	1.459 (4)	C5—N1	1.420 (4)
C2—H2	0.9500	N1—N2	1.260 (3)
C3—C4	1.355 (4)	N2—N3	1.122 (3)
C3—H3	0.9500
C2—C1—C5	123.1 (2)	C3—C4—S1	113.2 (2)
C2—C1—S1	113.34 (19)	C3—C4—H4	123.4
C5—C1—S1	123.5 (2)	S1—C4—H4	123.4
C1—C2—C3	107.1 (2)	O1—C5—N1	123.7 (2)
C1—C2—H2	126.5	O1—C5—C1	124.8 (3)
C3—C2—H2	126.5	N1—C5—C1	111.5 (2)
C4—C3—C2	114.3 (3)	N2—N1—C5	112.8 (2)
C4—C3—H3	122.8	N3—N2—N1	174.5 (3)
C2—C3—H3	122.8	C4—S1—C1	92.11 (14)
C5—C1—C2—C3	178.9 (2)	S1—C1—C5—N1	−0.6 (3)
S1—C1—C2—C3	−0.5 (3)	O1—C5—N1—N2	2.1 (4)
C1—C2—C3—C4	0.0 (3)	C1—C5—N1—N2	−178.0 (2)
C2—C3—C4—S1	0.5 (4)	C3—C4—S1—C1	−0.7 (3)
C2—C1—C5—O1	−0.1 (4)	C2—C1—S1—C4	0.7 (2)
S1—C1—C5—O1	179.2 (2)	C5—C1—S1—C4	−178.7 (2)
C2—C1—C5—N1	−179.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N1i	0.95	2.63	3.512 (4)	155
C3—H3···N3ii	0.95	2.66	3.396 (4)	135
C4—H4···O1ii	0.95	2.47	3.415 (4)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯N1i	0.95	2.63	3.512 (4)	155
C3—H3⋯N3ii	0.95	2.66	3.396 (4)	135
C4—H4⋯O1ii	0.95	2.47	3.415 (4)	173

Symmetry codes: (i) ; (ii) .